Yes, I know it probably seems like a jurassic technology, but I have a good reason for wanting to install DOS 5.0 under Parallels Desktop 14.0.1. However, I'm encountering an error and am hoping there might be someone who can suggest ideas. I'm using the method described in message #12 in the following thread (which was concerned with DOS 6.22, but same idea): https://forum.parallels.com/threads/ms-dos-vms.30679/ Starting at the Parallels Desktop, steps I'm taking: File > New Choose: "Install Windows or another OS from a DVD or image file" Continue Select File [Locate on Mac file system]: DOS5.0_bootdisk.iso Open [Message]: Unable to detect Operating System Continue [Message]: Please select your operating system Other > Other DOS OK [Enter name for .pvm]: DOS 5.0 Create [Message]: Amount of memory 32 MB outside recommended range. Change to maximum recommended amount? Don't change At this point, I get an A:\ DOS prompt. Based on the instructions in the message thread linked above, I gather I next need to create a DOS partition for a boot drive using fdisk, and format it with the "format /s" command. I therefore enter "fdisk" and see the fdisk menu. I select "Create DOS partition," then "Create primary DOS partition." When asked, I say I want to use the maximum available size and make the partition active. After this step, I see a message "System will now restart. Insert DOS disk in drive A:, Press any key" When the VM reboots, I see a message identifying the Parallels BIOS, a notice that 32 MB of physical memory is installed, Network bootrom installed. Then the following: Trying to boot from Primary Master IDE drive ... Missing operating system At this point I haven't figured out how to progress any further. Any suggestions on how to get past this point? Or is there another sequence of steps I should be using overall for the install?